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1,3-二苯基脲/β-环糊精衍生物包合物的表征、制备及对植物生长的促进作用

Characterization, Preparation, and Promotion of Plant Growth of 1,3-Diphenylurea/β-Cyclodextrin Derivatives Inclusion Complexes.

作者信息

Yamamoto Koki, Tanikawa Takashi, Tomita Junki, Ishida Yoshiyuki, Nakata Daisuke, Terao Keiji, Inoue Yutaka

机构信息

Laboratory of Nutri-Pharmacotherapeutics Management, Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama3500295, Japan.

Instrument Analysis Center, Josai University, 1-1 Keyakidai, Sakado, Saitama3500295, Japan.

出版信息

ACS Omega. 2023 Sep 13;8(38):34972-34981. doi: 10.1021/acsomega.3c04428. eCollection 2023 Sep 26.

DOI:10.1021/acsomega.3c04428
PMID:37779935
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10536069/
Abstract

The study aimed to prepare inclusion complexes of 1,3-diphenylurea (DPU) with β-cyclodextrin (βCD) and 2-hydroxypropyl-β-cyclodextrin (HP-βCD) using a three-dimensional ground mixture (3DGM). Their physicochemical properties, intermolecular interactions, solubilities, and plant growth-promoting activities were investigated on broccoli sprouts. Phase-solubility diagrams indicated the stability constant () and complexation efficiency (CE) of βCD/DPU were found to be = 250 M, CE = 2.48× 10. The and CEs of HP-βCD/DPU were found to be = 427 M, CE = 3.93 × 10 and = 196 M, CE = 1.93 × 10 respectively. The powder X-ray diffraction results of 3DGM (βCD/DPU = 2/1, HP-βCD/DPU = 2/1) showed that the diffraction peaks originating from the DPU and βCD disappeared, indicating a halo pattern. Differential scanning calorimetry results showed an endothermic peak at 244 °C derived from the melting point of DPU, but the endothermic peak disappeared in the 3DGM (βCD/DPU = 2/1, HP-βCD/DPU = 2/1). Near-infrared absorption spectra showed peak shifts in 3DGM (βCD/DPU and HP-βCD/DPU) at the -CH and -NH groups of DPU and the -OH groups of βCDs and free water. In the dissolution test (after 5 min), the concentration of intact DPU was 0.083 μg/mL. However, the dissolution concentrations of DPU in the 3DGM (βCD/DPU = 1/1), 3DGM (βCD/DPU = 2/1), 3DGM (HP-βCD/DPU = 1/1), and 3DGM (HP-βCD/DPU = 2/1) were 3.27, 3.64, 5.70, and 7.03 μg/mL, respectively, indicating higher solubility than that of the intact DPU. Further, H-H NOESY NMR spectroscopic measurements showed cross-peaks between H-A (7.32 ppm) and H-B (7.12 ppm) of DPU and H-6 (3.79 ppm) in the βCD cavity of the 3DGM (βCD/DPU = 2/1). A cross-peak was also observed among DPU H-A (7.32 ppm), H-B (7.11 ppm), and H-6 (3.78 ppm) in the βCD cavity. The results of the broccoli sprout cultivation experiment showed that 3DGM (βCD/DPU = 1/1), 3DGM (βCD/DPU = 2/1), 3DGM (HP-βCD/DPU = 1/1), and 3DGM (HP-βCD/DPU = 2/1) increased the stem thickness compared with that of the control group (DPU). These results indicated that the βCD/DPU and HP-βCD/DPU inclusion complexes were formed by the three-dimensional mixing and milling method, which enhanced the solubility and plant growth-promoting effects.

摘要

本研究旨在使用三维研磨混合物（3DGM）制备1,3 - 二苯基脲（DPU）与β - 环糊精（βCD）和2 - 羟丙基 - β - 环糊精（HP - βCD）的包合物。对西兰花芽苗菜研究了它们的物理化学性质、分子间相互作用、溶解度和促进植物生长的活性。相溶解度图表明，βCD/DPU的稳定常数（）和络合效率（CE）分别为 = 250 M，CE = 2.48×10。HP - βCD/DPU的和CE分别为 = 427 M，CE = 3.93×10和 = 196 M，CE = 1.93×10。3DGM（βCD/DPU = 2/1，HP - βCD/DPU = 2/1）的粉末X射线衍射结果表明，源自DPU和βCD的衍射峰消失，呈现晕圈图案。差示扫描量热法结果显示，在244℃处有一个源自DPU熔点的吸热峰，但在3DGM（βCD/DPU = 2/1，HP - βCD/DPU = 2/1）中该吸热峰消失。近红外吸收光谱显示，在3DGM（βCD/DPU和HP - βCD/DPU）中，DPU的 - CH和 - NH基团以及βCDs的 - OH基团和游离水处出现了峰位移。在溶解试验（5分钟后）中，完整DPU的浓度为0.083μg/mL。然而，3DGM（βCD/DPU = 1/1）、3DGM（βCD/DPU = 2/1）、3DGM（HP - βCD/DPU = 1/1）和3DGM（HP - βCD/DPU = 2/1）中DPU的溶解浓度分别为3.27、3.64、5.70和7.03μg/mL，表明其溶解度高于完整DPU。此外，H - H NOESY NMR光谱测量显示，在3DGM（βCD/DPU = 2/1）的βCD腔内，DPU的H - A（7.32 ppm）和H - B（7.12 ppm）与H - 6（3.79 ppm）之间有交叉峰。在βCD腔内的DPU H - A（7.32 ppm）、H - B（7.11 ppm）和H - 6（3.78 ppm）之间也观察到一个交叉峰。西兰花芽苗菜栽培实验结果表明，与对照组（DPU）相比，3DGM（βCD/DPU = 1/1）、3DGM（βCD/DPU = 2/1）、3DGM（HP - βCD/DPU = 1/1）和3DGM（HP - βCD/DPU = 2/1）增加了茎的厚度。这些结果表明，βCD/DPU和HP - βCD/DPU包合物是通过三维混合研磨法形成的，这增强了溶解度和促进植物生长的效果。

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